HCID 66604924, compound → HCID 178497266, compound

HRID 2410769Notes

Reaction equation

HRID 2410769 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)[CH:19]=[C:18]([C:29]([O:31][CH3:32])=[O:30])[C:14]=3[NH:15][C:16]=2[CH:17]=1)C1C=CC=CC=1>FC(F)(F)C(O)=O>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([C:20]2[CH:19]=[C:18]([C:29]([O:31][CH3:32])=[O:30])[C:14]3[NH:15][C:16]4[CH:17]=[C:9]([OH:8])[CH:10]=[CH:11][C:12]=4[C:13]=3[N:21]=2)=[CH:27][CH:26]=1

Participants

3

Reactant 1

HCID 66604924HCID 66604924, compound

Product 1

HCID 178497266HCID 178497266, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

An solution of methyl 7-(benzyloxy)-2-(4-chlorophenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (709 mg, 1.60 mmol) in trifluoroacetic acid (15 mL) was heated at 70° C. for 30 min. The solvent was removed and the residue was suspended in a mixture of EtOAc (25 mL) and hexane (50 mL). The suspended solid was collected by filtration and washed with the EtOAc/hexane mixture. This gave impure methyl 2-(4-chlorophenyl)-7-hydroxy-5H-pyrido[3,2-b]indole-4-carboxylate (573 mg). MS (ESI) m/z 353.0 (M+H).

Workup

  1. customThe solvent was removed
  2. additionthe residue was suspended in a mixture of EtOAc (25 mL) and hexane (50 mL)
  3. filtrationThe suspended solid was collected by filtration
  4. washwashed with the EtOAc/hexane mixture

Sources & evidence

ORD record
ord-2948877cebc6439d801e8acc23094edb
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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